Methylhydrazine → t-butyl alpha-[6(R)-amino-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

HRID 256022Notes

Reaction equation

[O:1]=[C:2]1[C@@H:8]([N:9]2C(=O)C3=CC=CC=C3C2=O)[CH2:7][S:6][CH2:5][C@@H:4]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[N:3]1[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].CNN>>[NH2:9][C@H:8]1[CH2:7][S:6][CH2:5][C@@H:4]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[N:3]([CH2:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C:2]1=[O:1]

Participants

Reactant 2

HCID 6061Methylhydrazine

HCID 13877949t-butyl alpha-[5-oxo-6(R)-phthalimido-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 13877951t-butyl alpha-[6(R)-amino-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetateYield 90%

Procedure

1.18 g of t-butyl α-[5-oxo-6(R)-phthalimido-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (f) above] was subjected to de-phthaloylization with methylhydrazine in the manner described in Example 1(g), to give 0.77 g of the title compound as an amorphous solid.

Sources & evidence

ORD record: ord-750faa63b1964cd599551fc02558990c
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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